Donald Trump asked former FBI Director James Comey about the possibility of jailing journalists and described a boast by Vladimir Putin about Russian prostitutes, according to Comey's notes of talks he had with the US president.
The 15 pages of documents obtained by The Associated Press contain new details about a series of interactions between Trump and Comey.
Those seven encounters in the weeks and months before Comey's May 2017 firing include a Trump Tower discussion about allegations involving Trump and prostitutes in Moscow.
They also include a White House dinner at which Comey says Trump asked him for his loyalty and an Oval Office discussion where the ex-FBI head says the president asked him to end an investigation into Michael Flynn, the former White House national security adviser.
Comey's interactions with Trump are a critical part of special counsel Robert Mueller's investigation into whether the president sought to obstruct justice.
Late on Thursday Trump tweeted that the memos "show clearly that there was NO COLLUSION and NO OBSTRUCTION."
The president also accused Comey of leaking classified information.
In explaining why he wrote the memos, Comey has said he "knew there might come a day when I would need a record of what had happened" to defend not only himself but the FBI as well.
The memos cover the first three months of the Trump administration which included revelations of an FBI investigation into potential ties between the Trump campaign and Russia.
In a February 2017 conversation Trump told Comey how Putin told him, "we have some of the most beautiful hookers in the world" even as the president adamantly distanced himself from a salacious allegation concerning him and prostitutes in Moscow, according to one memo.
In another memo, Comey recounts how Trump at a private White House dinner pointed his fingers at his head and complained that Flynn, his embattled national security adviser, "has serious judgment issues."
By that point, the FBI had already interviewed Flynn about his contacts with the Russian ambassador, Sergey Kislyak, and the Justice Department had already warned White House officials they were concerned Flynn was vulnerable to blackmail.
Flynn was fired on February 13, 2017, after White House officials said he had misled them about his Russian contacts by saying that he had not discussed sanctions.
The following day, according to a separate memo, Comey says Trump cleared the Oval Office of other officials, encouraged him to let go of the investigation into Flynn and called him a good guy.
Flynn pleaded guilty to lying to the FBI and is now cooperating with Mueller's investigation.
The memos also show Trump's continued distress at a dossier of allegations - compiled by an ex-British spy whose work was funded by the Democratic National Committee and the Clinton campaign - examining potential ties between him and his aides and the Kremlin.
Comey writes how Trump repeatedly denied to him having been involved in an encounter with Russian prostitutes in a Moscow hotel.
"The president said 'the hookers thing' is nonsense," Comey writes.
The documents also include the president's musings about pursuing leakers and imprisoning journalists.
Comey is on a publicity tour to promote his new book, A Higher Loyalty.